Enter The Stage: 25 Years Of Hip Hop At The MTV MTV Video Music Awards

In anticipation of Sunday's MTV VMA's, we look back at the top moments at MTV's Video Music Awards--from Run DMC to Ice-T, Kanye West & Taylor Swift.

Controversial. Unforgettable. Annual. These are merely three of the words that have frequently described popular music's most uproarious night of the year, the MTV Video Music Awards. With the 30th installment coming up on Sunday, August, 25 and emanating for the first time from Brooklyn, it’s only fitting since the Moonman’s launching pad is in one of Hip Hop’s dominant boroughs that we look back at Hip Hop’s history at the VMA’s.

Hip Hop has had a presence at the Video Music Awards since the very first show back in 1984. There, Herbie Hancock’s groundbreaking “Rockit” (which featured the then avant-garde practice of record scratching) video lead the night in terms of honors, taking home five Moonmen—two more than Michael Jackson’s “Thriller.” The next year, Run-DMC opened the show, explaining the process of how the awards were voted on, making them the first Hip Hop VMA performance. Despite this, it wouldn’t be until 1987 that a Rap video was nominated for a Video Music Award as their clip, “Walk This Way” lost in both “Best Stage Performance” and “Best Overall Performance” to Bon Jovi’s “Living on a Prayer” and Peter Gabriel’s “Sledgehammer” respectively. The next year the Fat Boys were joined by Chubby Checker to perform “The Twist,” and the live Hip Hop performance became a VMA staple.

Get It Started: MTV’s First Best Rap Video Award

The year 1989 saw the very first “Best Rap Video” award, presented by Fab 5 Freddy and Neneh Cherry given out as DJ Jazzy Jeff & The Fresh Prince’s “Parents Just Don’t Understand” beat out Ice-T’s “Colors,” Kool Moe Dee’s “How Ya Like Me Now,” MC Hammer’s “Turn This Mutha Out” and the night’s sole live Hip Hop performer Tone Loc’s “Wild Thing,” to take home the inaugural Hip Hop Moonman. The ‘90s began with MC Hammer breaking the Rap parameters and being the first Hip Hop video nominated under multiple categories, as his iconic “U Can’t Touch This” clip racked up five nominations and took home “Best Rap Video” and “Best Dance Video.”

That same evening, MC Hammer’s performance of “U Can’t Touch This” effectively stole the show, further cementing the Awards’ Hip Hop performances as one of the show’s greatest attractions. Years later, Snoop Dogg’s 1994 performance of “Murder Was The Case” not only graced the MTV airwaves with some of its most vivid, unforgettable imagery the network had ever broadcast, but carried over into the real life drama of evading arrest under suspicion of murder charges. But after death comes eternal life, as Bone Thugs-N-Harmony lit up the stage in 1996 with a career-defining performance of their monster hit “Tha Crossroads.” They left the award show empty-handed, losing in all five nominated categories.

Born Into The ‘90s: Bad Boy, Bone, Busta Rhymes & More

The late ‘90s saw Hip Hop become not only one of the most visible presences at the awards, but was responsible for some of the most memorable images both good and bad. Of course, 1997 was the year that saw the Bad Boy Family memorialize Biggie with the iconic Sting-assisted tribute “I’ll Be Missing You,” Busta Rhymes presented an award with Martha Stewart, and the first ladies of Hip Hop assembled for an extravagant performance of “Not Tonight (Ladies Night Remix),” highlighted by Da Brat rapping on a chariot. The very next year gave us the No Limit Soldiers making us say “Ugh,” Canibus in full silver body paint and ODB almost being blown up by on-stage pyrotechnics during Pras and Mya’s “Ghetto Superstar.” The millennium ended with the Run-DMC/Aerosmith/Kid Rock revisiting of “Walk This Way,” the Beastie Boys winning the coveted Video Vanguard Award and Lauryn Hill taking home the night’s top honors for “Video of the Year.”

But while the final awards of the ‘90s featured the unforgettable first public meeting of Tupac’s mother Afeni Shakur and Biggie’s mother Voletta Wallace, the next decade of VMAs would be most notable for the constant conflict. Between the 50 Cent and Fat Joe kerfuffle at the 2005 Awards, Kanye West and Lil Mama jumping on-stage at the most inappropriate times in 2009 and Eminem getting into a shoving match with comedian/hand-puppet Triumph, the Insult Comic Dog in 2002 (really, the only people Eminem seemed to ever get along with at these Awards were the Eminem clones that accompanied him for his 2000 “The Real Slim Shady” performance) the novelty of Hip Hop’s biggest stars under a formally informal roof predominantly lent itself to confrontation and controversy.

Bigger And Deffer: Hip Hop & The Future Of MTV’s Video Music Awards

Recent years have seen Hip Hop return to being one of the night’s most anticipated highlights. Kanye West began his road to redemption on the way to My Beautiful Dark Twisted Fantasy with his performance of “Runaway” in 2010—a year also memorable for will.i.am’s all-black jumpsuit attire becoming among the most bizarre get-ups in the show’s history. It’s a fashion choice that can only be described as Canibus-esqe. According to MTV and Nielsen, 2011 served as the most watched Video Music Awards ever, giving us the genuinely touching moment of Odd Future’s Tyler, the Creator winning the Best New Artist award and giving one of the most heartfelt speeches in the show’s history. While last year’s show was most memorable for host Kevin Hart pitching 2 Chainz the idea of wearing three chains and Young Money’s reaction shots, MTV seems to be pulling out all the stops for the show’s return to New York this year at the Barclay Center. Here’s to 30 more years of hip-hop shining on MTV’s biggest platform.

Chaz Kangas is a freelance journalist covering music, film and pop culture's highbrow and low-brow. He's contributed to the New York Times, Village Voice, LA Weekly, Citypages and Complex among others. Originally from Minneapolis, MN but currently residing in Harlem, NY, he's also guest-lectured at Sarah Lawrence College and Fairfield University and is currently co-authoring R.A. the Rugged Man's autobiography. You can follow him on twitter @ChazRaps